1. Field of the Invention
The present invention relates to a catalytic chemical process for making .beta.-aminopropionamides. Such compounds are particularly useful derivatives in further preparing cationic vinyl monomers useful in preparing flocculants, adhesion promoters, oil soluble dispersions, epoxy curing agents and ion exchange resins.
2. Description of the Prior Art
It is well-known that amines will react with acrylic or methacrylic esters to form .beta.-aminopropionamides. Thus, for example, certain .beta.-aminopropionamides compounds can be made by reacting dialkyl amine compounds with an acrylic acid or ester compound, as described in the article by J. G. Erickson, "The Preparation and Stabilities of Some .beta.-dialkylaminopropionamides", J. Am. Chem. Soc. 74, 6281-82 (1952).
Aminolysis of esters is also described by J. F. Bunnett and G. T. Davis, J. Am. Chem. Soc. 82, 665 (1960) and H. T. Openshaw and M. Whittaker, J. Chem. Soc. 89, (1969). Other processes leading to compounds of this type are set out in U.S. Pat. Nos. 2,451,436; 2,529,838; 2,649,438; and 3,652,671.
As set out in U.S. Pat. Nos. 2,719,175 and 2,719,178 the resultant .beta.-aminopropionamides can then be broken down by heat to give monomeric compounds.
Other work of this type is described by H. L. Bassett and C. R. Thomas, J. Chem. Soc. 1188 (1954) in German Pat. No. 1,164,397.
However, normally the reaction between an amine and an acrylic or methacrylic ester will proceed only slowly at moderate temperatures. One can elevate the temperature to complete the reaction and form the desired propionamide but then side reactions become significant.
In order to promote the reactions between esters and amines use of certain compounds have been suggested. For example, in the article by H. L. Bassett and C. R. Thomas, J. Chem. Soc. 11, 1188 (1954) the use of stoichiometric quantities of an alkylmagnesium halide has been described. While such compounds have been found to act as an aid in forming amides, it was also found that catalytic quantities were not effective here. In yet another route in producing acrylamides from acrylic esters and amides the use of lithium hydroxide and magnesium methoxide as catalysts were proposed (German Pat. No. 1,164,397).
However to date no simple method has been found to form .beta.-aminopropionamides from acrylic or methacrylic esters and the appropriate amines, which can be run at relatively low reaction temperatures, and which results in few side products compared to the prior art. Some catalysts, for example, in this area may catalyze the desired reaction, and likewise promote undesired side reactions.
It would therefore be an advantage in the art to provide a new catalytic method for preparing .beta.-aminopropionamides, which reaction could be run at relatively low reaction temperature and would produce few quantities of undesired side products.